2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 135819173, compound

HRID 322972Notes

Reaction equation

HRID 322972 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[C:15]1[O:16][CH2:17][CH:18]([C:20]([O:22][CH3:23])=[O:21])[N:19]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[C:15]1[O:16][CH:17]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[N:19]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 135819174HCID 135819174, compound

Product 1

HCID 135819173HCID 135819173, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 2-[2-hydroxy-4-(3-thienylmethoxy)phenyl]-4,5-dihydrooxazole-4-carboxylate (1 g) and (2,3-dichloro-5,6-dicyanobenzoquinone (0.8 g) in toluene (100 mL) is stirred at reflux for 2 hours. The reaction is concentrated in vacuo and the residue passed through a pad of silica eluting with 20% ethyl acetate in cyclohexane. The eluant is concentrated in vacuo and the residue partitioned between ethyl acetate (100 mL) and 1N HCl (50 mL). The organic phase is washed with water (20 mL), dried over magnesium sulphate and concentrated in vacuo to give methyl 2-[2-hydroxy-4-(3-thienylmethoxy)phenyl]oxazole-4-carboxylate (400 mg).

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe reaction is concentrated in vacuo
  3. concentrationThe eluant is concentrated in vacuo
  4. customthe residue partitioned between ethyl acetate (100 mL) and 1N HCl (50 mL)
  5. washThe organic phase is washed with water (20 mL)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbafe0b067b8482aae7037c9bde44c85
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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